HCID 68183820, Verbindung → HCID 68184017, Verbindung

HRID 879014Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879014
[Cl:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([O:17]C)=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[C:7]([CH3:19])=[N:6]1.[Br-].[Br-].[Br-].B>C(Cl)Cl>[Cl:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([Cl:1])[C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([OH:17])=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[C:7]([CH3:19])=[N:6]1

Komponenten

4

Edukt 2

HCID 68183820HCID 68183820, VerbindungHCID 178419136HCID 178419136, Verbindung

Produkt 1

HCID 68184017HCID 68184017, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of the compound [179](7.4 mg) in methylenechloride (0.2 mL) was added 1M methylenechloride solution of borane tribromide (0.2 mL) under ice-cooling, and then the reaction mixture was stirred at 0° C. for 3 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by reverse phase preparative liquid chromatography to give the titled compound (3.7 mg) as a pale brown solid.

Aufarbeitung

  1. temperaturecooling
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by reverse phase preparative liquid chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6bf9455997394067a6ef658c6334f17a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987473B2

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